1-Diazidocarbamoyl-5-azidotetrazole, often jokingly referred to as azidoazide azide,^[5] is a heterocyclic inorganic compound with the formula C₂N₁₄.^[6] It is a highly reactive and extremely sensitive explosive.

1-Diazidocarbamoyl-5-azidotetrazole was produced by diazotizing triaminoguanidinium chloride with sodium nitrite in ultra-purified water.^[6] Another synthesis uses a metathesis reaction between isocyanogen tetrabromide in acetone and aqueous sodium azide.^[3] This first forms isocyanogen tetraazide, the "open" isomer of C₂N₁₄, which at room temperature quickly undergoes an irreversible cyclization reaction to form a tetrazole ring.^[7]

The C₂N₁₄ molecule is a monocyclic tetrazole with three azide groups. This ring form is in equilibrium with isocyanogen tetraazide, an isomeric acyclic structure that has long been known to cyclize quickly to the tetrazole.^[7]

It is one of a family of high energy nitrogen compounds in which the nitrogen atoms do not have strong triple bonds. This instability makes many such compounds liable to explosive decomposition, releasing nitrogen gas.

This tetrazole explosive has a decomposition temperature of 124 °C. It is very sensitive, with impact sensitivity lower than 0.25 joules. It is, however, less sensitive than nitrogen triiodide. Decomposition can be initiated by contact or using a laser beam.^[8] For these reasons, it is often erroneously claimed to be the world's most sensitive compound.^[9][5]

• The dictionary definition of azidoazide azide at Wiktionary